Hey pill poppers, I'm in my twenties. I reached out to an old classmate from middle school after she liked a few of my photos on a site. We chat, jokes back and forth. She says she'd be willing to travel a few hours to meet with me once she gets settled. I escalated by saying shed like my room layout. She followed saying she had to go to sleep.

In retrospect, I think I should have stopped once she said be willing to travel to see me. Any advice for knowing when to escalate/when to stop in the future?